methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside | 40653-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside
• CAS: 40653-16-5
• 化学式: C₃₀H₃₄O₆
• 分子量: 490.596
• InChiKey: KNRKAILSTGGYJM-ZNOUKXQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以75%的产率得到methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-formyl-α-D-mannopyranoside
  参考文献：
  名称：

  General Homologation Strategy for Synthesis of l-glycero- and d-glycero-Heptopyranoses

  摘要：

  A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

  DOI：

  10.1021/acs.orglett.5b02620
• 作为产物：
  描述：

  ((2R,3R,4S,5S,6S)-3,4,5-三(苄氧基)-6-甲氧基四氢-2H-吡喃-2-基)甲醇 在 2-碘苯甲酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.0h， 生成 methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside
  参考文献：
  名称：

  General Homologation Strategy for Synthesis of l-glycero- and d-glycero-Heptopyranoses

  摘要：

  A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

  DOI：

  10.1021/acs.orglett.5b02620